How To Build An Antifragile Career

When the economic future feels more iffy than ever, randomness should not be something to fear but rather, something to exploit. Author-provacateur Nassim Taleb talks with Fast Company about the concepts behind "Antifragile: Things That Gain from Disorder" and how we can harness disorder to advance our careers and our companies.

Nassim Nicholas Taleb likes to pick fights. Tim Geithner, Alan Greenspan, Paul Krugman: all catch the ire of the trader-turned-scholar, as these economists failed to anticipate the financial crisis, while Taleb, sensing the fragility of Fannie Mae—and the financial industry in general—did. And in so doing, made millions.

The crisis was the kind of extreme event that he described in The Black Swan, his 2007 investigation into the power of volatility, that for its pugilistic prescience earned Taleb fame and infamy. In Antifragile, Taleb is still fighting—oranges, soccer moms, and the federal reserve are all lambasted (the first is "Mediterranean candy," the other two protective to the point of harm), and he’s still prescient, the kind of thinker that in his vigor is able to shift a reader’s worldview, though his mission is simple.

"I want to live happily in a world I don't understand," he writes in the prologue to Antifragile, a paean to randomness. "You get pseudo-order when you seek order; you only get a measure or order and control when you embrace randomness."

The antifragile—his coinage—is what embraces randomness and its cousins, volatility and time. We’re familiar with objects that don’t like volatility—consider your nearest piece of porcelain—and things that for their robustness can withstand change, like the Brooklyn Bridge. But there isn’t even a word, Taleb would have us know, for that which actually benefits from disturbances. That's the antifragile: a fine pair of leather shoes, your body (think exercise and vaccines), and evolution have it.

The other key piece of the Antifragile puzzle is linearity and its prefixed sibling, nonlinearity. The linear is familiar: One plus one does equal two, except when it doesn't; the function of a doubled amount can be far greater. Taleb likes the illustration of either a 10-pound rock being thrown or 10 pounds of pebbles being heaved at you. That's what he'd call "accelerated damage," the kind he learned of in Fannie Mae.

It's in one's interest to know if one is vulnerable to the volatility of accelerated damage—fragility—or of the rarer accelerated benefit, antifragility, or otherwise robust to change. This managing of vulnerabilities forms the core of Taleb's thought, and it has many business applications. Which is why Fast Company was eager to correspond with Taleb about a few of the topics we're most passionate about: career choices, the nature of entrepreneurship, and what business strategy looks like in an opaque world (a hint: it looks a lot less like theorizing, a lot more like tinkering).

But it's not just for the celebrities. Taleb advocates bimodal strategies in working life: to have one very stable gig and one volatile vocation by moonlight.

"Never go for medium profession," he told Fast Company via email. "Literary writers should have a menial job or (if possible) a sinecure, and write on the side. Otherwise writing for a living under other people's standards debases their literature. The same for artists. The best philosophers were not academics, but had another job, so their philosophy was not corrupted by careerism."

Literature, art, philosophy: These are fields where the successful (whatever the measure of success is) are a relative (and daresay random) few, so to have a robust but not mentally taxing day job is an asset. But what about your everyday business people?

To get a picture of how randomness plays a role in professional life, Taleb compares two brothers: one an office worker, the other a taxi driver. Volatility is present in the career of each: while the office worker has randomness "smoothed away" by the regularity of salary and employment, he is like a turkey in mid-November, fragile to risk presently out of view. On the other hand, the taxi driver—who Taleb describes as being of the class of artisan, much like a carpenter or plumber—experiences a natural randomness in his daily fluctuations of fares, but is less prone to large shocks. Indeed, Taleb writes, the self-employed artisan can be antifragile: a weeklong earnings decline tells the taxi driver to try a new part of town, while a mistake made in the cubicle farm will be kept on the permanent record. As well, the office worker has one main employer and thus rigidity, while the taxi driver has many—giving him more options, greater flexibility to adapt to his environment.

To get an idea of how the individual contributes to the ecosystem, consider the dining scene in Manhattan: While the odds are dim if you want to make it as a restaurateur, they’re bright if you’re looking for a bite to eat. To put it in Taleb’s terms, the fragility of the individual contributes to the robustness, or even antifragility—if the group is evolving and not staying the same—of the whole. "We need to respect failed entrepreneurs," he tells Fast Company. "This would make more people take risks and generate growth." At the end of the fourth chapter of the book, he proposes a National Entrepreneur Day, one furnished with this message:

"Most of you will fail, disrespected, impoverished, but we are grateful for the risks you are taking and the sacrifices you are making for the sake of the economic growth of the planet and pulling others out of poverty. You are the source of our antifragility. Our nation thanks you."

Beyond rippling with Taleb's signature bombast, the quote makes a fair point, one that he rephrases elsewhere in the book: that just as there's no such thing as a failed soldier (so long as he fights with courage), there's no such thing as a failed entrepreneur, even if the company goes belly up. All those failed East Village eateries ensure that you've got the right place for Friday night; "What kills me makes others stronger," he says, in the same way that the deaths of individuals help along evolution.

So what does an optionality-based strategy look like for a company? Some thinkers are already on the way. Connected Company coauthor Dave Gray has a game plan for turning an enterprise into an engine of possibility; Click Moment author Frans Johansson exhorts "the wisdom of small bets," speaking of the effectiveness of creating a minimal viable product that interacts with the random—and serendipitous—forces of the market, allowing us to live happily in a world we don't understand, unlike that contented turkey in mid-November.

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You can also work yourself to death trying to be antifragile. Obsessive pursuit of goals can drive you onto all sorts of mental illness situations. No one can be good at everything, all the time. Be driven, be inspired, but also be sure to relax every once in a while.

In the grandeur scheme of things we do very little to nothing for that very little guy. Entrepreneurs pollinate so many different areas in so many different ways. But they probably get the least amount of help from the get go (contingent on where an entrepreneur lives). Combined with that fact (very little support) 100% entrepreneurs go through an era where they feel like they are constantly staring into the abyss and chewing glass (to quote Elon Musk). Entrepreneurs can positively transform the world in so many different ways. But it requires that we encourage them to fail. But at the same time, we come up with a mechanism that allows us to measure and evaluate, so that the system of provision does not get compromised and misused.